Boron tribromide → HCID 178519046, compound

HRID 747873Notes

Reaction equation

HRID 747873 reaction equation
BrC[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13]C)=[CH:10][CH:11]=2)[O:6][C:5](=[O:15])[C:4]=1[C:16]1[C:17]([O:24][CH3:25])=[N:18][C:19]([O:22]C)=[N:20][CH:21]=1.B(Br)(Br)Br>C(Cl)CCl>[OH:22][C:19]1[N:20]=[CH:21][C:16]2[C:4]3[C:5](=[O:15])[O:6][C:7]4[C:12](=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=4)[C:3]=3[CH2:25][O:24][C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 115822324-Bromomethyl-3-(2,4-dimethoxy-pyrimidin-5-yl)-7-methoxy-chromen-2-one

Product 1

HCID 178519046HCID 178519046, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-bromomethyl-3-(2,4-dimethoxy-pyrimidin-5-yl)-7-methoxy-chromen-2-one (200 mg, 0.492 mmoL) in ClCH2CH2Cl (5 mL) at room temperature was added BBr3 (1.0 N, 2.50 mmoL, 2.5 mL). The result reaction mixture was stirred at room temperature for 30 min and then heated to reflux overnight. The reaction was cooled down and the solvent was removed in vacuo. The residue was dissolved in 10% K2CO3 in MeOH:acetone (˜1:1, 10 mL) at 0° C., stirring was kept for another 2 hours. The solvent was evaporated to dryness, the residue was dissolved in water (15 mL) and then acidified with dilute hydrochloric acid to about pH 4. The precipitated brown solid was isolated by filtration, washed with water and dried to yield the title compound.

Workup

  1. customThe result reaction mixture
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe reaction was cooled down
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in 10% K2CO3 in MeOH:acetone (˜1:1, 10 mL) at 0° C.
  7. stirringstirring
  8. waitwas kept for another 2 hours
  9. customThe solvent was evaporated to dryness
  10. dissolutionthe residue was dissolved in water (15 mL)
  11. customThe precipitated brown solid was isolated by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-6956c664bf8c4de58330ee02216264c9
Source dataset
uspto-grants-2008_07
Patent number
US07399767B2

Reaction notes

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